3,5-difluoro-N,N-dimethyl-4-(2-methylphenyl)aniline | 1392440-69-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-difluoro-N,N-dimethyl-4-(2-methylphenyl)aniline
• CAS: 1392440-69-5
• 化学式: C₁₅H₁₅F₂N
• 分子量: 247.288
• InChiKey: YTPBTZDMQSAEFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,5-二氟-N,N-二甲基苯胺 在 potassium phosphate 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 1,2,3,4,5-五苯基-1′-(二叔丁基膦)二茂铁 、 4,4'-二叔丁基-2,2'-二吡啶 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 36.0h， 生成 3,5-difluoro-N,N-dimethyl-4-(2-methylphenyl)aniline
  参考文献：
  名称：

  A C–H Borylation Approach to Suzuki–Miyaura Coupling of Typically Unstable 2–Heteroaryl and Polyfluorophenyl Boronates

  摘要：

  A method for the synthesis of biaryls and heterobiaryls from arenes and haloarenes without the intermediacy of unstable boronic acids is described. Pinacol boronate esters that are analogous to unstable boronic acids are formed in high yield by iridium-catalyzed C-H borylation of heteroarenes and fluoroarenes. These boronates are stable in the solid state or in solution and can be generated and used in situ. They couple with aryl halides in the presence of simple palladium catalysts, providing a convenient route to biaryl and heteroaryl products that have been challenging to prepare via boronic acids.

  DOI：

  10.1021/ol301570t

文献信息

• A C–H Borylation Approach to Suzuki–Miyaura Coupling of Typically Unstable 2–Heteroaryl and Polyfluorophenyl Boronates
  作者：Daniel W. Robbins、John F. Hartwig

  DOI：10.1021/ol301570t

  日期：2012.8.17

  A method for the synthesis of biaryls and heterobiaryls from arenes and haloarenes without the intermediacy of unstable boronic acids is described. Pinacol boronate esters that are analogous to unstable boronic acids are formed in high yield by iridium-catalyzed C-H borylation of heteroarenes and fluoroarenes. These boronates are stable in the solid state or in solution and can be generated and used in situ. They couple with aryl halides in the presence of simple palladium catalysts, providing a convenient route to biaryl and heteroaryl products that have been challenging to prepare via boronic acids.